Awesome vid and so thankful that this is available. Just a quick question - when at 2:30 we say that the carboxylic acid on the right is unstable - is it also fair to say that it's a strong acid (so reactive/unstable) as a result of the Beta carbonyl being electron withdrawing? Or is it specifically because of that kinda ring formation that gets made.
The lack of stability is referring to the fact that beta keto acids (with the C=O on the beta carbon) break down readily in heat in comparison to other carboxylic acids. The reason for this is that we form the cyclic concerted transition state as a result of the H being spatially close to the carbonyl as mentioned. You could think of the beta carbonyl as being withdrawing as the electrons are moving in that direction in the mechanism of the reaction, but it is a part of the bigger picture.
For the malonic ester synthesis, what is the in-depth reason why we need to use NaOEt? If we hydrolyze the esters, does it matter if they got converted to O=C-OMe esters using NaOMe?
This is the best explanation and comparison of these processes that I've found, as usual. Thank you, Chad!
You're welcome and Thank You!
your explanations are always through and incredibly comprehensive!!
Glad you think so - Thanks!
This was amazingly helpful in comparing/contrasting these processes - thank you!!
You're welcome, Amanda - glad it helped!
thank u so much sir, you are honestly the best teacher out there..
Thanks! Great to have you here :)
Awesome vid and so thankful that this is available.
Just a quick question - when at 2:30 we say that the carboxylic acid on the right is unstable - is it also fair to say that it's a strong acid (so reactive/unstable) as a result of the Beta carbonyl being electron withdrawing? Or is it specifically because of that kinda ring formation that gets made.
The lack of stability is referring to the fact that beta keto acids (with the C=O on the beta carbon) break down readily in heat in comparison to other carboxylic acids. The reason for this is that we form the cyclic concerted transition state as a result of the H being spatially close to the carbonyl as mentioned. You could think of the beta carbonyl as being withdrawing as the electrons are moving in that direction in the mechanism of the reaction, but it is a part of the bigger picture.
For the malonic ester synthesis, what is the in-depth reason why we need to use NaOEt? If we hydrolyze the esters, does it matter if they got converted to O=C-OMe esters using NaOMe?
Great work, Chad!
Thank you, Ben!
thank you for these videos
You are welcome!
Thank you for making this make sense to me! SOOO helpful!
You're welcome, SS!